Leading Through Uncertainty: Pivoting a Startup With Transparency

When you’re leading a startup, uncertainty isn’t an occasional visitor, it’s a constant presence. But sometimes, the market shifts in ways you can’t predict. At Alohome, we’ve experienced this firsthand. As a proptech company serving homebuilders, we built solutions to address their marketing challenges and accelerate their success. Yet, when market conditions changed drastically, we faced an uncomfortable truth: The market we had committed to was no longer as viable as we hoped.

Interest rates spiked, housing demand slowed, permits became more complicated, and construction activity fell. Homebuilders pulled back on investments, making it clear that our business model needed to adapt. Some of our clients went bankrupt, others simply called us and told us they literally couldn’t afford to purchase their own domain. On top of that, the fundraising environment had shifted dramatically, with capital becoming harder to secure. As leaders, we had tough decisions to make.

This is the story of how we navigated those challenges, led with transparency, and found the strength to pivot — even when motivation was hard to come by. While we haven’t yet figured out our fundraising path, we remain committed to adapting, learning, and keeping our operations going.

Recognizing When It’s Time to Pivot

One of the hardest parts of leadership is recognizing when what you’re building is no longer the best path forward. For months, we held on, hoping that market conditions would recover. We launched some very powerful AI products, we adjusted our pricing, we built new partnerships in new markets, and made everything to cut costs. But no amount of operational tweaking can change the reality of a sick market.

The turning point came when our once super-healthy cash flow started to increase in accounts due month after month. Our clients were simply going under at a fast pace; we were still closing the largest accounts in our history, but despite all that progress, we were still in the same place because of churn. Our once-promising growth had stalled. Conversations with our customers confirmed what we feared: homebuilders were simply not in a position to invest in our solution. No matter how well we executed, the fundamental market tailwinds had become headwinds.

As a founder, it’s tempting to push through with optimism. But clarity came when we asked ourselves a different question: If we weren’t already building this, would we choose to start it today? The answer was, not really. This was really tough, but it put us in contact with the reality of a changing industry. 

Transparency as a Leadership Tool

Facing the truth was one thing — sharing it with the team was another. I’ve learned that transparency isn’t just about delivering bad news, it’s about trusting your team with the reality of the situation. When leaders are open about challenges, it fosters a culture of shared responsibility.

We held several all-hands meetings to lay out the facts as things were unfolding. I shared the market data, the challenges we faced, and the options we had. It wasn’t a monologue — it was a conversation. The team’s response was so humbling. There was disappointment, of course, but also resilience. People wanted to know how they could help. This is to me one of the biggest lessons I’ve learned and will always be grateful for the team for always trusting me,Michael Meo, and each other to do the best we can. 

This openness allowed us to tap into the collective intelligence of the team. Some proposed adjacent markets we could explore. Others suggested internal shifts to extend our runway. When people feel included in decision-making, they’re far more committed to seeing it through. The camaraderie and morale went through the roof: We are in this together. 

We’ve extended this same transparency to our investors. Instead of pretending everything is fine, we’ve been upfront about the challenges we’re facing and our plan to pivot. As a first time founder, this has been one of the most challenging areas for me.  On the one hand, the reality of a business that is having challenges, and on the other, the hope to save face and the responsibility for the money of people that have trusted us with their money. While it hasn’t resulted in immediate solutions, my hope is to lean into the unknown and build long-term trust.

Navigating the Emotional Toll

Pivoting a startup is not just a business decision, it’s deeply personal, and it's deeply emotional. First is the sense of losing; it is a heavy weight that needs to be put in check because there is urgent work to be done. As leaders, we carry a responsibility for others, our team, our clients, our investors, and it is easy to lose track of our needs and well-being. There are days when I question whether we were making the right choice, and I’ve caught myself second guessing all of my business choices. Sleeping becomes challenging, anxiety starts to become present, and there is, for me, this sense of failure. The uncertainty weighed heavily on all of us.

Motivation became fragile. The adrenaline that once came from chasing growth was replaced by the anxiety of the unknown. As a leader, I realized I couldn’t ignore these feelings — my own or those of the team.

What helped was acknowledging the emotional toll out loud. I spoke openly about my own doubts and frustrations. Creating space for others to do the same brought us closer together. For me, leaning into my co-founder with transparency, vulnerability, and a sense of humor has been incredible. We also made it a point where we could celebrate small wins — a successful experiment, positive customer feedback, or even a constructive debate. These moments reminded us why we were still fighting. And my wife, my family, and my friends have backed me in so many ways that all I can say is, THANK YOU.

Committing to a New Unknown

Once we aligned on the need to pivot, the next step was committing fully. We explored adjacent markets where our technology could add value. We also revisited our core strengths: understanding buyer journeys, building AI-driven tools, and super-serving clients. We are moving faster and faster every week.

It wasn’t a linear path. Some experiments failed. Others revealed opportunities we hadn’t considered before. Every two weeks, we gathered to assess what was working and what wasn’t. The transparency we had built early on became our biggest advantage. The team felt empowered to take risks, knowing that failure was part of the process.

While the markets, our future, and the fundraising environment remains uncertain, we are doing everything we can to keep the business operational, maximize our resources, and demonstrate clear progress. And most importantly, we’re staying open to learning together.

A Message to Other Founders

If you find yourself in a similar position, know this: you’re not alone. Many founders are quietly struggling with the same challenges. Some are facing tough pivots. Others are winding down. Some are running a brutal race against the clock with diminishing runways. The pressure can feel isolating, but the reality is that uncertainty is part of this journey.

Be honest with your team. Be honest with your investors. And be honest with yourself. Lean into transparency, embrace the discomfort, and remember that the toughest moments often lead to the greatest growth. Lean into the team that trusts you; we are in this adventure together.

And if you’re a founder who’s already been through this, consider reaching out to others in the trenches. Your insights and support can make all the difference.

We may not have all the answers, but we’re committed to finding them — together.